How to Be More Strategic as a Leader
Creating and cascading objectives into the work your team does every day
“Be more strategic.”
It’s common feedback as leaders move into more senior roles. It’s also not particularly helpful if you don’t know what doing that differently actually looks like. If you’re trying to figure out how to be more strategic as a leader, one practical place to start is with how you create alignment.
If I were stepping into a VP role today, I wouldn’t spend my first week auditing the tech stack or redrawing the org chart.
Tempting, but not the best opening move for someone shifting more of their time to working ON the business.
At this level, you’re expected to elevate your strategic thinking, establish your executive presence and sharpen your decision-making. Those can feel like pretty abstract expectations.
How to Be More Strategic as a Leader: Start With Alignment
Can you draw a clear line from what the company is trying to accomplish to the work happening across your organization every day?
More importantly, can your leaders draw that line?
Once you’re leading through managers of managers, you can’t create alignment through your own communication alone. Your leaders need to understand what you’re trying to accomplish, why it matters, what it means for their teams, and how the work they do contributes.
The best way I've found to create alignment within your orgamization, and with your Frist Team, is through greating and sharing your cascading objectives. I learned the principles of cascading objectives early in my career at HP. I’ve adapted them many times since, but the basic idea has stayed with me:
Objectives cascade down. Results build up.
Cascading objectives turns strategy into execution
Cascading objectives doesn’t mean taking the company goal and giving everyone underneath you a smaller version of it. You have to be strategic.
It means translating the company’s objectives into what your function needs to accomplish, the strategies you’ll use to get there, how you’ll measure whether those strategies are working, and ultimately the work and decisions your teams make every day.
The model I use looks like this:
Going down the model, you’re translating strategy into increasingly specific action.
Going back up, you should be able to explain how that work produces the results the business needs.
That second direction matters just as much.
If you can’t trace a piece of work back to an objective or strategy, it’s worth asking why you’re doing it.
What cascading objectives looks like in practice
When I joined Snowflake in 2019 to lead North America Professional Services, one of the company priorities was revenue growth. For Professional Services to contribute, we needed to help new customers get to meaningful consumption faster.
That translated into an objective for our organization: reduce the time to meaningful consumption for new customers. From there, we could define the strategy, then we could identify the measures that would tell us whether it was working. But the work wasn’t the same for everyone.
Same objective. Different teams. Different work.
And now each team had a much clearer answer to a question that matters:
How does what I do contribute to what the company is trying to accomplish?
Create consistency around strategy and flexibility around execution
The model becomes more fluid as you move down it.
Company and functional objectives need consistency. Your strategies need enough stability to give the organization direction. This is where constantly introducing another good idea can become a distraction.
Closer to the work, I want more flexibility.
Once people understand the objective, strategy and measures, those closest to the work should have room to figure out how to get there. They often have some of the best ideas about what should change, what isn’t working and what could be done differently.
That distinction matters.
Alignment shouldn’t mean telling everyone exactly what to do. It should give people enough clarity to make good decisions without needing the executive in every decision.
Strategic alignment has to work across the organization
A function can hit its own objectives and still create problems elsewhere in the business.
So I wouldn’t consider the cascade complete until my leaders had looked across the organization, too.
Who do we depend on? Who depends on us? Where could our objectives or measures compete? What resources or decisions require another team? What needs to be solved together?
Some of the most important alignment conversations happen horizontally, not vertically.
Why AI makes strategic clarity even more important
AI dramatically expands what teams can do.
We can generate ideas, analyze data, create content, experiment and execute faster than we could before. That creates enormous opportunity.
It also creates a lot more possible work.
The ability to do something faster doesn’t answer whether it is the right thing to do.
Clear objectives and strategy give people a way to evaluate all that new capacity. Which objective does this support? What measure should it move? Why is this worth doing now?
AI can accelerate the work. Leaders still have to create the clarity that helps an organization choose where to apply that acceleration.
Working ON the business means looking further ahead
This is another part of the transition into more senior leadership that can be difficult to make concrete.
You don’t stop working IN the business when you become a VP. You still need to know what’s happening this week, this month and this quarter. You still need to know where the business is off track and where a decision or intervention is needed.
But increasingly, you also have to work ON the business.
If we continue on this trajectory, where will we be six months from now?
Are we seeing enough movement today to deliver the results we’ll need then?
What will the organization need six or twelve months from now that it doesn’t have today?
Which other teams do we need to engage now?
The more senior the role, the further ahead some portion of your attention needs to go.
10 questions to test strategic alignment
If you’re leading a function—or preparing to—I’d start by seeing how clearly your organization can answer these questions:
What is the company trying to accomplish?
What does our function need to contribute or deliver?
What strategies have we chosen, and why?
How will we know they’re working?
What operating processes support the work?
What decisions and work do our teams own, and where do they have flexibility?
Who do we depend on—and who depends on us?
How does our work drive business results?
What work are we doing today that no longer supports our objectives?
How do we share progress across the team?
And then I’d test it somewhere other than the leadership team.
Ask someone in a skip-level conversation what the organization is trying to accomplish, why it matters and what it means for their team.
Can they explain it?
Can they explain how their work contributes?
That tells you quite a bit about whether the strategy has actually made it through the organization.
